Most Shocking Celebrity Exes: Guess Who I Dated

Can you guess who your favorite celebs dated before they met "The One"?

The Fresh Princess

1/28

Clue: In the early ‘90s, before The Fresh Prince of Bel Air married his queen, Jada Pinkett-Smith, he dated quite a few princesses. This particular princess went on to create a “bankable” industry all her own. Can you guess who he’s posing with here?

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Will Smith Once Dated...

2/28

Answer: Tyra Banks.

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Rock With Me

3/28

Clue: When it comes to walking the red carpet, rocker Lenny Kravitz has always been The Man. Although, when he chose to pose for pictures with this high profile diva, he’d certainly met his match.

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Lenny Kravitz Once Dated...

4/28

Answer: Naomi Campbell.

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Onscreen Romance

5/28

Clue: Actress Sanaa Lathan has had many onscreen love interests in the past, but when she went one-on-one with this guy for a film, he quickly stole her heart in real life. He went on to find the “total” package he was looking for in someone else.

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Sanaa Lathan Once Dated...

6/28

Answer: Omar Epps.

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Young Love

7/28

Clue: Before Long before Nick Cannon and ex wife Mariah Carey tied the knot he was another songstress’ dream guy. (And her love didn’t cost a thing.) Their split was the first of two high-profile breakups for the songbird, and now the biggest love of her life is a baby girl, age 4.

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Nick Cannon Once Dated...

8/28

Answer: Christina Milian.

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The Odd Couple

9/28

Clue: Halle Berry has a lot of memorable exes in her past, but few know about her old romance with this guy. Today, men go wild for Ms. Berry, but back in the late 80s, female fans were crazy for this ex, and Berry was just the new kid on the block.

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Halle Berry Once Dated...

10/28

Answer: Former New Kids on the Block band member Danny Wood.

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Low Profile Love

11/28

Clue: Back when Boomerang star Robin Givens began dating this future A-list hunk they kept such a low profile that to this day many people have no clue they were ever an item.

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Robin Givens Once Dated...

12/28

Answer: Brad Pitt.

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Making Whoopi

13/28

Clue: Whoopi Goldberg rules the daytime talk show circuit now, but back in the ‘90s, she ruled this actor’s heart. After filming a romantic comedy together in 1993, this pair couldn’t fight the chemistry they shared. By the time the film hit theaters, they could be seen out in public hand-in-hand.

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Whoopi Goldberg Once Dated

14/28

Answer: Ted Danson.

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Catwalk Queen

15/28

Clue: Supermodel Tyra Banks had this sexy singer on her arm years before he met and married another catwalk queen.

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Tyra Banks Once Dated...

16/28

Answer: Seal.

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High School Crush

17/28

Answer: When it came time to choose the perfect prom date, Brandy made a very tall order. Back then a young Brandy just couldn’t resist this rookie’s charm, and for a short time they were an “It” couple. Since then, he has gone on to become one of the greatest athletes of all time. (But we’re not telling which one!)

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Brandy Once Dated...

18/28

Answer: Kobe Bryant.

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Lo and Behold

19/28

Clue: This big city diva caught Wesley Snipes’ attention long before she became one of America’s biggest (and highest paid!) stars. Can you guess who?

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Wesley Snipes Once Dated...

20/28

Answer: Jennifer Lopez.

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Thug Love

21/28

Clue: Did you know, the lovely Vivica Fox once fell for one of the industries most infamous bad boys? They never made it to marriage (or had any baby millionaires) but back when they posed for this photo, they were all smiles.

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Vivica A. Fox Once Dated...

22/28

Answer: 50 Cent.

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My First Love

23/28

Clue: Guess who first captured singer Ciara’s heart long before NFLer Russell Wilson? Here’s a hint: He’s a PYT for sure, but he’s definitely not “lil” anymore.

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Ciara Once Dated...

24/28

Answer: Bow Wow.

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We've Got Something In Common

25/28

Clue: Common is flying solo these days, but admits that this sporty sister (pun intended!) used to have his heart. Sadly, things didn’t end as he'd hoped, but he still has nothing but love for this superstar.

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Common Once Dated...

26/28

Answer: Serena Williams.

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A Song For You

27/28

Clue: This one should be easy. When Ray J fell for this famous fashionista, their infamous hookup landed them in nationwide headlines, and many say, eventually catapulted her to super stardom. These days, she is a paparazzi darling, really famous and happily married (with two beautiful babies) to an equally huge star.